Why Everyone Is Into Ugly Fashion: An Explainer

I was casually strolling through SoHo one weekend when I passed a man — a tourist, I presume — gesturing obnoxiously at the Prada flagship display window as he said, in a voice dripping with a mix of horror and disdain, "This, all of this — hideous." Not in the mood to leap to Miuccia Prada's defense, I moved on. About a week later, I passed by the Gucci flagship on Fifth when another man — another tourist, likely — was staring at the luxury brand's latest looks when he shook his head, defeated, and shrugged: "I don't get it." Around that time, a "Last Week Tonight with John Oliver" segment aired in which the British host openly mocked a badass tiger-embroidered fringed black leather jacket by Gucci, incredulously wondering who would shell out $6,000 for this aesthetically offensive article of clothing. Um, I would? You know, if I had a few thou to spare.

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It's true that these were all cis males and stereotypical gender norms dictate that they don't know what they're talking about, so we could chalk it up to their straight-male fashion ignorance. You could also argue that these designers were doing their job at successfully man-repelling, another indicator that Serious Fashion was hard at work here. But I'd argue there's more to it: an entire brand of peacocking that's become embedded in our cultural zeitgeist. It's this desperation to be unique, to stand out in the ocean of style stars, that has spawned a sartorial genre that many outside our fashion bubble — including these three gentlemen — would deem "ugly."

This "ugliness" has manifested itself in rigid retro jeans that are neither comfortable nor flattering (the wedgie-inducing style that punches out just a smidge, with a waist that's a touch too high), clunky shoes, frame-swallowing silhouettes, mismatched maximalism, and excessive finishes (by way of ruffles, shine, beadwork, etc).

A look from Prada's Fall 2016 collection. Photo: Imaxtree

But wait, isn't ugliness subjective? Well, yes, yes it is.

"Beauty is in the eye of the beholder, but 'ugly fashion' means 'not the mainstream' — it's not what everyone's wearing, it's not what the general population deems as 'in' right now," says Megan Collins, a trend forecaster from Trendera, a firm that analyzes trends through a generational lens. "The conversation between fashion, beauty and ugliness has always existed, but this is the first time we live in a culture where so many people are taking part in this conversation."

There is a difference, though, between ugly fashion and ugly clothing, which celebrity stylist Dani Michelle (who dresses Bella Thorne, Lucy Hale and Kourtney Kardashian) pointed out. "Ugly fashion speaks toward a certain trend, decade or design that may not be the most flattering nor aesthetically stunning in the moment," she explains, using her recently purchased "so ugly, but so fabulous" purple Preen lamé metallic drawstring dress as an example. "Ugly clothing is just badly designed garments."

So why are we all suddenly into ugly fashion? How did we get here? There are many influencing factors feeding into the overarching movement, but the first can be traced back to the rise of normcore, the anti-fashion attitude that, ironically, became fashionable about three years ago. Coined by trend-forecasting agency K-Hole, normcore sparked the now-ubiquitous extraordinarily average mom/dad jean- and Birkenstock/white sneaker-wearing uniform.

"There was a definite spike in ugly fashion because of normcore," Collins confirms. "Coupled with the rise of Instagram and popularity of fashion bloggers, it really took off. I think now, more than ever, influencers have to go to more and more extremes to set the trend, because people are picking it up so fast — it's becoming mainstream so fast — so they have to go further and further to feel different."

"Oh my god, it's crazy — there's so much pressure that there are days when I'm like, I can't anymore. I started this for fun, but now, I have to post constantly and in doing that, I'm going to lose what makes me special, because I have to keep pulling shit out of my ass," she says candidly, going on to describe herself as a magpie, whose aesthetic is part retro, part eclectic. "I'm lucky and I appreciate it, but there's so much noise — fashion has become so democratic. Your resources used to only be in New York, London, Milan, and Paris, but now, just look on Instagram and everyone is stylish — and if everyone is stylish, then how do you stand out from that? You go the other way."

And it's exacerbated by an overwhelming fear of and aversion to being basic (in other words, to be mainstream). It's the ultimate insult to a fashion insider. "You are ostracized in this industry for being basic," says Sara Holzman, fashion editor at Marie Claire. "I'm terrified of basicness," Whittington echoes.

"We live in a world where our lives are constantly on display and you don't want to be seen as just like everyone else — we are so concerned with building a personal brand that's unique, special and has a different perspective, so when someone calls you basic, it's tearing down your whole brand and everything that you've worked so hard to build," Collins says. "I also think more people are dressing for themselves (versus men or society), so they are very careful about what they're buying and what it says about them. It's also why everyone wants something customized — it's special, unique, and we're just more narcissistic than ever."

Of course, it helps that designers are supplying these outrageously out-there pieces to fulfill this social media-driven demand, like Vetements and its roster of buzzy collaborations (Juicy Couture onesies, Manolo Blahnik "bants," and Levi's bare-butt jeans for starters), Balenciaga's silhouette-manipulating shapes or Gucci's sparkling alien unitard. Stars aren't immune to sartorial controversy, either: There was Kendall Jenner and her puzzling janklets, and more recently, Millie Bobby Brown killing it in Topshop's infamous jindows.

But as pervasive as it is on street style, social media and the runways, how body-inclusive is ugly fashion? "There are these beliefs that women with bigger sizes have to only wear clothes that are flattering, that they have to follow the rules — but that doesn't have to be true," says Lauren Chan, former plus-size model who's currently the fashion features editor at Glamour. "Plus-size fashion is not directional in the way a lot of great ugly-fashion pieces are, but I think uniqueness can be achieved with vintage and thrifted fashion. I wear oversize pieces, menswear and mom jeans all the time, all of which would be considered ugly by a lot of people who are dictating what clothing should look like for plus-size women. It's perceived as ugly because it's different."

Different, yet at the same time, suspiciously familiar — because at the root of ugly fashion is an undercurrent of '90s influence. It's the result of fashion's cyclical nature and, interestingly enough, Gen Z-er's fascination with the decade.

"We're seeing, for the first time, the younger generation is heading up the trends versus the trends trickling down, so teenagers will love something and then millennials will pick them up, because they're so obsessed with being young and cool," Collins explains. "So with fashion, we're seeing teens reaching back into the past for prevalent labels that were popular in the '90s."

The '90s came to an end eventually — and so, too, will ugly fashion, just like every trend before it. So once ugly fashion becomes mainstream, it will inevitably flip. And at today's rate of trend turnovers, that might be sooner than we think.

"When any new trend comes out, people hate it, but eventually, everyone loves it — the Internet is just making the cycle go much faster," Whittington says. "I personally love having a unique expression, because without ugly fashion and diversity, we'd all look the same. I appreciate anything that's out of the norm, even if the rest of the world is like, what the hell is going on here?"

Athletic, orthopedic and downright dorky sandals are popping up on the feet of some of the coolest girls I know. We're not just talking about Adidas shower sandals: Tevas and Birkenstocks are also becoming favorites.
Yes, this is a real thing.

Karl Lagerfeld, a man nearly as famous for his one-liners as the clothes he designs for Fendi and Chanel, took the stage with actress Jessica Chastain at New York's Lincoln Center for an hour-long interview Wednesday night.